How Anna Cleveland Is Emerging as a Model in Her Own Right

While most models are plucked from obscurity and thrust into the spotlight, the industry is increasingly a family business. Many of the young women and men currently stomping down the catwalk—Gigi Hadid, Georgia May Jagger, and Ella Richards among them—have parents whose work paved the way for their careers. The business relies literally on good genes, but having a model parent comes with pitfalls as well as advantages. No one knows this better than Anna Cleveland, the elegant daughter of model Pat Cleveland, a seminal figure of the ’70s fashion scene and continued presence in the photographs of fellow icons like Bruce Weber. Known for her effervescent personality and energetic performances on the catwalk, Pat was a muse to everyone from Halston to Yves Saint Laurent. And now there’s also 26-year-old Anna, who walked 20 shows on the Spring runways and who, with her aquiline nose and lithe physique, instantly calls to mind her mother—a fact that proves daunting at times. “My mother is inspiring, but her legacy carried a lot of weight,” says Cleveland. “Being her daughter, I thought, Is [modeling] her thing, or is this my thing? In many ways, it’s been harder for me in this business because I have to distinguish myself.”

Cleveland’s first editorial shoot occurred at the age of 2. “I had the Duchess of Windsor’s diamonds in my mouth!” she says over tea at the Soho Grand. Animated and quick to joke, Cleveland recounts tales from her childhood with a storyteller’s flair. Walking down the Moschino runway at age 5 and appearing alongside her mother on Karl Lagerfeld’s runway at 13 aren’t typical childhood experiences, but they were part and parcel of an upbringing steeped in fashion history. “I remember meeting [Franco Moschino] and seeing the balloons in the air at the end of the show and just feeling that energy,” she says. “Or walking for Karl for the first time with my mom! Getting to have those experiences as a family was something special.” Growing up an hour from Milan amid the pastoral beauty of Stresa, Lago Maggiore, Italy, however, Cleveland spent most of her time out of the limelight, but her brief forays in front of the camera left a lasting impression. “I was going to events at an early age, so I’d get completely in it, and then get to take a step back into reality. You have to have the yin and yang. It’s fantastic to be completely submerged in fashion, but so important to find your Zen space and replenish.”

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Photographed by Phil Oh

2015 has given Cleveland the opportunity to plunge even deeper into the industry she holds dear. Signing with Next Management and taking on modeling full-time after several years of stops and starts, she’s quickly established herself as a runway fixture—but not without some key advice from her mother. “My mom told me last year, ‘You will find people who get who you are, and once you do it will change everything,’ ” says Cleveland. “She was right. This year has been such a blessing. I think my view on the business is a little different because I’ve had my mother here as a mentor and chaperone.” Walking 20 shows this season, Cleveland proved herself adept at handling Fashion Week’s pace and capable of creating a bona fide runway moment. Her spirited twirl down the catwalk for Moschino was both a refreshing change of pace and a welcome throwback to the days when models weren’t afraid to get zany. For Cleveland, it was all about bringing the designer’s vision to life: “Some people think that I’m a person who always wants to do a performance on the runway, but [Jeremy Scott] said, ‘Do your thing and just fly.’ ”

Taking Scott’s advice and running with it is indicative of the way Cleveland approaches modeling: It isn’t a job as much as an opportunity for collaboration. Before she walks or poses, she begins with a step many models forget: asking the designer or photographer exactly what they’re looking for. “When you work, you’re entering their world, and you get just to bounce ideas off each other,” she says. “Together you create an image, a story, a persona. I enjoy when the process is intimate. When you’re genuinely interested in knowing that person, you can connect on a better level.” Designers have responded warmly to Cleveland’s approach—Jeremy Scott, Zac Posen, and Jean Paul Gaultier have all referred to her as a muse, a title she embraces wholeheartedly: “You have to take it as a compliment. It’s a beautiful thing when they call me that; all I want is to inspire and be inspired.”

Even when she isn’t on the job, Cleveland’s interests align with those of her profession. She loves jazz, which can be not unlike the controlled chaos of backstage; her habit of mood-boarding her shoots speaks to a potential for a fashion career behind the scenes. And she’s a film buff with an appreciation of the silent period, identifying with that era’s acting icons, like Greta Garbo and Clara Bow. “I find that I can relate to them because they’re doing an ‘unspoken’ job,” she says. “It’s about communicating without words, and as a model I draw inspiration from that.” Given her in-demand status, the model hasn’t had much time to indulge in her hobbies lately, but at the moment she’s content to experience everything life has to offer—as long as it involves her primary passion, that is. Says Cleveland: “I’ve tried living without fashion. I can’t do it. I live for the moment—I think we all do, and that’s why we’re in fashion!”